A seasoned Real Estate Attorney would know the answers to all of those questions and more and there is no conflict of interest when it comes to advising you.

One high season week and it pays for itself.

I have an unfurnished property in Florida that needs to be furnished and ready to go for seasonal rentals for 3-9 month rental periods.

Do BRRRR on steroids, where you act as your own HML and get your 100% money back within a month (not the whole seasoning period).

A seasoned CPA with REI experience can help ensure all your passive losses are applied correctly and provide guidance on future sales.

Someone suggested we ask them to be out by Oct 1 so that we get a new tenant before the holiday season. 

We're going to do a mid-term/seasonal rental in the house, and a long term rental in the "caretaker" trailer.

That's a great way to put it.Hi Guys,Yes, that will be the move, I already know and have sketch of 2 ways to do it, I didn't want to get into a crazy rehab now, till I make sure my contractor is a team player and he will be able to do so, my idea is to add SF and create a master sweet, let's see if the numbers work fist, this is something I will do after the property is stabilized, I think I can get my capital back and some more with the 3/1 layout now, I will keep you posted!

You want to break down your preference in regard to sale price, down payment, program, (SFR/MFH), seasoning is important, and the two R's you want to pay most attention to is the Renovate and Refinance.Most investors make the mistake on the renovate or refinance and sometimes both.You also have to figure out if your buying as a Primary or investment because if you buy as a primary you always refinance before you rent. 

This is not nay saying, urinating on or being negative, this is seasoned STR investors not wanting others to fail.